


Cry for me

by daddyquest



Category: Cry Wolf (2005), Supernatural
Genre: Barebacking, Dacryphilia, Daddy Kink, Dirty Talk, Fingering, M/M, Praise Kink, Riding, Rimming, Sam in an oversized hoodie riding Benny, Sam is a good boy, Secret Relationship, benny is a headmaster, sam is an 18 year old student, sammy is a whiny lil thing during sex, teacher student relationship
Language: English
Status: In-Progress
Published: 2016-07-15
Updated: 2016-10-06
Packaged: 2018-07-24 05:42:08
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,009
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7496052
Author URL: https://archiveofourown.org/users/daddyquest/pseuds/daddyquest
Summary: <blockquote class="userstuff">
              <p>Sam is a student at a boarding school, Benny is his headmaster. Benny and Sam have sex on a regular basis and Sam has a penchant for whimpering and crying real tears during sex.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So I was watching Cry Wolf and Jared looked really fucking good in that school boy outfit and blue hoodie so I started thinking about Benny as his headmaster. I'm a sick fuck. See y'all in hell.

**Summary for the Chapter:**

> Sam rides Benny in an oversized hoodie.

Sam whimpers when Benny gently thrusts up driving his cock further up into him. They're on Sam's bed in his dorm, Benny, the headmaster, is laying back against the bed being slowly ridden by eighteen year old student Sam.

When Sam's dorm mate had left to go get dinner with a friend he had called Benny and told him to come over, that he missed him, that he needed him badly and he needed it now. Benny was over in a flash ready to oblige. 

They didn't have time to fully undress, given the fact that this was a quickie in all regards. Benny was wearing a white button down, and black socks while Sam was wearing only his oversized blue hoodie rolling his hips straddling Benny's lap, bouncing a little.

"Getting greedy there, ain't ya?" Benny sighed digging his fingernails into Sam's hips. "Trying to get as much inside as you can, huh? Ain't that right sweetheart?" 

Sam bit his lower lip and nodded slowly. "Yeah," he whined. 

"Missed me didn't you?" Benny said. "Been weeks since you've had me fill you up. Hmm?" He reached behind the younger man tracing Sam's hole stretched wide around his thick cock. "How empty you must've felt this past month. Poor baby." 

"Missed it so much," Sam sighed, his eyes watering. He cried every time he got his hole fucked. He was very sensitive and his emotions got the best of him. Tears streamed down his cheeks and Benny gently wiped them away, loving so much how much his boy got into this. How he craved it so much that his emotions couldn't contain the pleasure. 

Sam's sleeves were so long they covered his hands and he gripped the ends making sweater paws against Benny's chest. "So much." He gasped as Benny gave one particularly slow but rough thrust.

"Say it," Benny cooed rubbing Sam's naked thighs. "You know I love when you say it. Be a good boy. C'mon, sugar." 

"Daddy," Sam whimpered. "Fuck me, Daddy. So full." His whiney sounds would put a professional porn star to shame. 

"That's it," Benny praised him. "Got me so hard, baby boy. You feel how hard you make me? Feel me throbbing inside you? C'mon now. Tell me, sweetheart." 

"So thick, Daddy," Sam sighed. "I'm so full. Making me ache. I need to cum. I'm so close. Please?" 

Sam's cock was completely covered by the oversized hoodie and had gone completely untouched since he had started riding Benny. "Let me get a peak at ya," Benny said. "See just what we're talkin' about." Benny slowly lift up the bottom of Sam's hoodie. Sam was hard and leaking against his own stomach. "Wow. You're a big boy ain't ya?" Benny said wrapping his thick hand around Sam's cock and gently pumping it, his other hand guiding Sam's hip movements helping him continue to ride him. "Such a big boy. You lookin' like you're ready to burst. You're such a nasty boy, loving that cock in your ass so much. Got you so hard. Filthy. Daddy loves his slut." 

Sam was shivering now, squeezing his sweater paws even hard and panting. "Daddy, please," he whined. 

"Let go, love," Benny cooed. "Show Daddy how much you enjoy being full. How it makes you cum having a cock inside your pretty little hole. C'mon." 

Sam's eyes shut and he bounced gently on Benny's cock twice before he was cumming, his cock dribbling inside Benny's milking hand. 

"Good," Benny said. "Good good good." He pet Sam's thighs reiterating how good he was over and over. "Came just like a girl. Maybe next time you can wear a skirt and be daddy's girl. Would you like that?" 

Sam collapsed forward so that he and Benny were chest to chest. Benny spread Sam's legs further as he lay on top of him and continued to gently fuck up into him. He came while Sam was whimpering "daddy" over and over again softly in his ear. 

Their breathing fell into sync as they lay together post orgasm, Sam spread out on top of his headmaster. Benny pulled out gently allowing his cum to leak from Sam's used hole into his bed sheets as he continued to kiss Sam's face in praise. 

"Daddy?" Sam said.

"What is it, sugar?" Benny said rubbing Sam's bare back under his hoodie. 

"I think next time I do want to be Daddy's girl," Sam blushed and hid his face in Benny's neck. 

"Atta boy."


	2. Chapter 2

**Summary for the Chapter:**

> The origin of how the relationship between Sam the student and Benny (Mr. Lafitte) the Headmaster transpired.
> 
> Featuring a mini fic in between it all of Benny rimming Sam.

**Notes for the Chapter:**

> I hope you enjoy! This is first time mixing past and present tense! I hope I did okay!

Sammy is a whiner. That's Benny's favorite thing about him. The way Sam cries actual tears when he's being fucked, how he makes sounds that are akin to that of a female porn star, how he gets so desperate that he begs and pleads and will do anything for Benny.

He's perfect. 

-  
They met the first day Sam had transferred to the posh little boarding school. Benny remembered that day like it was yesterday, the 17 year old orphan accompanied by his social worker for orientation and personal meeting with him, Benny, the headmaster. 

Benny promised the social worker, a fifty-something-year-old woman that he would take good care of Sam and see that he received the best education he possibly could.

It wasn't every day that a ward of the state received admission to such a prestigious institution, but here he was. Sam was very smart, yet another thing Benny loved about the boy. Sam worked his ass off to get accepted, which was his goal, purely to get more freedom. He would have his own bedroom, that enough was worth all the hard work. 

The first time Benny saw Sam he thought of him as a good looking kid but that was all. He wasn't a creep nor a predator. The kid was underage and was probably a broken little soul. The academy didn't have any single mother children much less any orphans up until that point. It was all inhabited by rich snobby kids with rich asshole fathers. Sam would be an outcast, Benny felt sorry for him. He promised to keep a close eye on him.

-

Benny underestimated how close of an eye he would be keeping on Sam, given the fact that his tongue was halfway inside of Sam now, bouncing his head between Sam's cheeks making the now 18 year old boy sob. Sam's face was covered in tears, his cheeks and neck soaking wet. 

"That's some pretty crying, baby boy," Benny sighed, the heat of his breath against his skin down there sending a shiver through Sam's body. "Use your words, now. Let Daddy know how you're feeling." 

"S-good," Sam whimpered, covering his face with the blanket. 

"Ah ah ah," Benny said, reaching up to gently remove the blanket from his face. "There will be none of that. You know how much I love watching you fall apart." 

-

Weeks had passed and Sam was getting more and more acclimated to the school by the day. Benny was happy to see that the other students figuratively embraced him with open arms and treated him like one of the crew. He really fit in. He had friends, real friends! He had even superseded the most popular students in the school and became the big shot on campus. Girls were throwing themselves at him, and every boy on campus wanted to be him. 

Much to Sam's shock, the entire student body threw Sam a surprise birthday party for his eighteenth. Benny remembered seeing the look of overwhelming happiness and belonging. He cried, but not nearly as much as he had that night, during his first time with Benny. 

He had walked up to Sam to congratulate him while he was eating his cake in the party hall. Slapping a big hand on the boy's shoulder, he expressed his happiness for Sam having fit in so easily. Sam blushed at the touch and thanked him. He looked at up Benny with shy eyes and coy smile. That was the trigger, that's what caused Benny to see him in the current light in which he saw him. 

Benny's breath caught in his throat. It was at that moment that he realized how beautiful the boy was, and the way Sam was looking up at him, he was sure Sam's thoughts were not so innocent. 

"I have to run to the bathroom, guys," Sam smiled. The table groaned in protest and three girls told him in succession to hurry back. 

Sam made a minute gesture with his head signaling Benny to walk with him. They didn't walk together, but rather three feet apart, acting as if they were going about their own business separately. Once inside the bathroom Sam turned to Benny and smirked. Benny used his master-key to lock the door. 

"It's very comical," Sam said crossing his arms and smiling. 

"What is?" Benny asked nervously. He had no idea what had overcome him to have locked himself in the bathroom with a student. An 18 year old student, granted, but a student none-the-less. 

"Those girls think they stand a chance with me," Sam said with a laugh. "They're pretty enough. But my tastes are a little more," he looked Benny up and down. "Rugged." 

"Sam," Benny said. He hadn't expected anything to actually happen, he figured they would get to the bathroom and talk. But here Sam was all but physically throwing himself at him. 

"Mr. Lafitte," Sam cocked his eyebrow. 

"You know we can't do this, right?" Benny said. 

"Do what?" Sam feigned confusion, ending his sentence with a smirk. 

"Whatever your pretty little head is fantasizing about," Benny said, taking the liberty to truly look Sam up and down for the first time, his stare languid. He looked so good. If only he were a few years older and not enrolled in his institution. 

"Do you what the best thing about growing up in an orphanage is, Mr. Lafitte?" Sam said stepping closer to the headmaster. 

"What?" Benny breathed. 

"I've come across many people and I've learned how to keep a secret when I need to," Sam's body was inches from Benny's now. His hand firmly pressed on Benny's chest. 

"Sam," Benny managed to sigh out before Sam leaned in to kiss him. 

\- 

Four months later found them in Benny's bed, Sam's legs pushed up so his knees pressed against his own chest while Benny ate him out torturously slow. Benny pulled the blanket from Sam's face just in time to see a new tear fall from his eye. 

Benny reached up to gather that tear from Sam's face onto his finger. He then began rubbing at Sam's hole with it, rubbing his tear against his opening. "Pretty little tears for a pretty little pussy," Benny cooed.  


Sam whimpered and rolled his hips, grinding down on Benny's thick digit. 

"Stay still," Benny said. "You're so squirmy today." He left a lingering peck on the inside of Sam's butt cheek. "My sweet sensitive boy. Wrecked little face. So desperate, Daddy adores you so much. Wish you could sleep in my bed every night." 

It was Christmas break and all the kids had gone home for the Holidays. Sam however, seeing as how he had no home, had lied to the school and said he was staying with his social worker and her family for the next two weeks but in actuality had been secretly staying in Benny's campus condo. 

"Daddy's little kept boy for the next two weeks. Not allowed to leave the house, can't let anyone see you. You're all mine, isn't that right, baby?" Benny pressed two more fingers in. Sam gasped and nodded enthusiastically. 

"All for you, Daddy," Sam whined. 

Benny continued fucking his hole slowly with his fingers as he climbed up to kiss the young man's lips, a faint taste of salt from his tears came with it. He stared down at Sam in awe. With his other hand he pushed Sam's hair back so he could see his beautiful face more clearly. 

"You're the best Christmas present I could have ever gotten."


End file.
